反応 #164166

反応方程式

(R)-quinuclidin-3-ol

DCC

Phenyl-(3-trifluoromethoxy-phenylamino)-acetic acid hydrochloride

HOBT

→

title compound

収率 86.0%

phenyl-(3-trifluoromethoxy-phenylamino)-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

収率 86.0%

溶媒

THF

反応条件

後処理

1. 1
   ろ過PS-DCC is filtered off
2. 2
   その他the filtrate is evaporated
3. 3
   workup.DISSOLUTIONThe resulting residue is dissolved in EtOAc
4. 4
   洗浄washed with water, sat. NaHCO3, water and brine
5. 5
   乾燥The organic phase is dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   その他evaporated

実験手順

PS-DCC (920 mg, 1.15 mmol, loading: 1.25 mmol/g) is suspended in THF (15 mL). Phenyl-(3-trifluoromethoxy-phenylamino)-acetic acid hydrochloride (I40) (200 mg, 0.57 mmol) and HOBT (176 mg, 1.15 mmol) are added, followed by (R)-quinuclidin-3-ol (219 mg, 1.73 mmol) and the mixture is shaken for 16 hours at RT. PS-DCC is filtered off and the filtrate is evaporated. The resulting residue is dissolved in EtOAc and washed with water, sat. NaHCO3, water and brine. The organic phase is dried over Na2SO4, filtered and evaporated to give the title compound as a colorless oil (206 mg, 85% yield, mixture of diastereoisomers).

出典